Stabilization and encapsulation of photosensitive resveratrol within yeast cell

International Journal of Pharmaceutics

Volumn 349, Issue 1-2, 2008, Pages 83-93

  Shi, Guorong ^a   Rao, Liqun ^a   Yu, Huazhong ^b   Xiang, Hua ^c   Yang, Hua ^a   Ji, Runa ^a  

^a HUNAN AGRICULTURAL UNIVERSITY   (China)

^b JISHOU UNIVERSITY   (China)

^c Hunan Administration School   (China)

Author keywords

Bioavailability; Microencapsulation; Resveratrol; Stability; Yeast cells

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; RESVERATROL; SCAVENGER;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STORAGE; DRUG STRUCTURE; ENCAPSULATION; FLUORESCENCE; FLUORESCENT LIGHTING; HUMIDITY; INFRARED SPECTROSCOPY; MOUSE; NONHUMAN; PHOTOSENSITIVITY; PRIORITY JOURNAL; RAT; SIMULATION; STOMACH JUICE; SUSTAINED RELEASE PREPARATION; TEMPERATURE; YEAST CELL;

BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DELAYED-ACTION PREPARATIONS; DRUG COMPOUNDING; DRUG STABILITY; DRUG STORAGE; FREE RADICAL SCAVENGERS; HEAT; LIGHT; MICROSCOPY, CONFOCAL; MICROSCOPY, FLUORESCENCE; PARTICLE SIZE; PICRATES; POWDERS; SACCHAROMYCES CEREVISIAE; SOLUBILITY; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STILBENES;

EID: 37349092988     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.07.044     Document Type: Article

References (81)

1. Abert Vian M., Tomao V., Gallet S., Coulomb P.O., and Lacombe J.M. Simple and rapid method for cis- and trans-resveratrol and piceid isomers determination in wine by high-performance liquid chromatography using Chromolith columns. J. Chromatogr. A 1085 (2005) 224-229
2. Aggarwal B.B., Bhardwaj A., Aggarwal R.S., Seeram N.P., Shishodia S., and Takada Y. Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Res. 24 (2004) 2783-2840
3. Asensi M., Medina I., Ortega A., Carretero J., Bano M.C., Obrador E., and Estrela J.M. Inhibition of cancer growth by resveratrol is related to its low bioavailability. Free Radic. Biol. Med. 33 (2002) 387-398
4. Barbosa M.I.M.J., Borsarelli C.D., and Mercadante A.Z. Light stability of spray-dried bixin encapsulated with different edible polysaccharide preparations. Food Res. Int. 38 (2005) 989-994
5. Belguendouz L., Fremont L., and Gozzelino M.T. Interaction of transresveratrol with plasma lipoproteins. Biochem. Pharmacol. 55 (1998) 811-816
6. Bertelli A.A.E., Giovannini L., Stradi R., Urien S., Tillement J.P., and Bertelli A. Kinetics of trans- and cis-resveratrol (3,4′,5-trihydroxystilbene) after red wine oral administration in rats. Int. J. Clin. Pharmacol. Res. 16 (1996) 77-81
7. Bhat K.P.L., Lantvit D., Christov K., Mehta R.G., Moon R.C., and Pezzuto J.M. Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Cancer Res. 61 (2001) 7456-7463
8. Bhat K.P.L., and Pezzuto J.M. Cancer chemopreventive activity of resveratrol. Ann. NY Acad. Sci. 957 (2002) 210-229
9. Bishop J.R.P., Nelson G., and Lamb J. Microencapsulation in yeast cells. J. Microencapsul. 15 (1998) 761-773
10. Blanquet S., Garrait G., Beyssac E., Perrier C., Denis S., Hébrard G., and Alric M. Effects of cryoprotectants on the viability and activity of freeze dried recombinant yeasts as novel oral drug delivery systems assessed by an artificial digestive system. Eur. J. Pharm. Biopharm. 61 (2005) 32-39
11. Blanquet S., Marol-Bonnin S., Beyssac E., Pompon D., Renaud M., and Alric M. The biodrug concept: an innovative approach to therapy. Trends Biotechnol. 19 (2001) 393-400
12. Bradamante S., Barenghi L., and Villa A. Cardiovascular protective effects of resveratrol. Cardiovasc. Drug Rev. 22 (2004) 169-188
13. Cappellaro C., Baldermann C., Rachel R., and Tanner W. Mating type-specific cell-cell recognition of Saccharomyces cerevisiae: cell wall attachment and active sites of a- and alpha-agglutinin. EMBO J. 13 (1994) 4737-4744
14. Choi H.K., Yang J.W., and Kang K.W. Bifunctional effect of resveratrol on the expression of ErbB2 in human breast cancer cell. Cancer Lett. 242 (2006) 198-206
15. Ci Y.X., Zang K.S., and Gao T.Y. FTIR study of microbes. Chem. J. Chin. Univ. 6 (2002) 1047-1049
16. Counet C., Callemien D., and Collin S. Chocolate and cocoa: new sources of trans-resveratrol and trans-piceid. Food Chem. 98 (2006) 649-657
17. Dardelle G., Normand V., Steenhoudt M., Bouquerand P.E., Chevalier M., and Baumgartner P. Flavour-encapsulation and flavour-release performances of a commercial yeast-based delivery system. Food Hyd. 21 (2007) 953-960
18. de la Lastra C., and Villegas A.I. Resveratrol as an anti-inflammatory and anti-aging agent: mechanisms and clinical implications. Mol. Nutr. Food Res. 49 (2005) 405-430
19. Delmas D., Jannin B., and Latruffe N. Resveratrol: preventing properties against vascular alterations and ageing. Mol. Nutr. Food Res. 49 (2005) 377-395
20. Feuillat M. Yeast macromolecules: origin, composition, and enological interest. Am. J. Enol. Viticul. 54 (2003) 211-213
21. Fremont L. Biological effects of resveratrol. Life Sci. 66 (2000) 663-673
22. Gao L.Y., Chu Q.C., and Ye J.N. Determination of trans-resveratrol in wine, herbs and health food by capillary electrophoresis with electrochemical detection. Food Chem. 78 (2002) 255-260
23. Gehm B.D., McAndrews J.M., Chien P.Y., and Jameson J.L. Resveratrol a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 14138-14143
24. Gosslau A., Chen M., Ho C.T., and Chen K.Y. A methoxy derivative of resveratrol analogue selectively induced activation of the mitochondrial apoptotic pathway in transformed fibroblasts. Br. J. Cancer 92 (2005) 513-521
25. Gouin S. Microencapsulation: industrial appraisal of existing technologies and trends. Trends Food Sci. Technol. 15 (2004) 330-347
26. Gürbüz O., Göçmen D., Da{eth}delen F., Gürsoy M., Aydin S., Sahin I., Büyükuysal L., and Usta M. Determination of flavan-3-ols and trans-resveratrol in grapes and wine using HPLC with fluorescence detection. Food Chem. 100 (2007) 518-525
27. Gusman J., Malonne H., and Atassi G.A. A reappraisal of the potential chemopreventive and chemotherapeutic properties of resveratrol. Carcinogenesis 22 (2001) 1111-1117
28. Hagerman A.E., Rice M.E., and Ritchard N.T. Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin16 (4 → 8) catechin (procyanidin). J. Agric. Food Chem. 46 (1998) 2590-2595
29. Haslam E. Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action (1998), Cambridge University Press, Cambridge
30. Hsieh T.C., Wang Z., Hamby C.V., and Wu J.M. Inhibition of melanoma cell proliferation by resveratrol is correlated with upregulation of quinone reductase 2 and p53. Biochem. Biophys. Res. Commun. 334 (2005) 223-230
31. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W., Fong H.H., and Farnsworth N.R. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275 (1997) 218-220
32. Jannin B., Menzel M., Berlot J.P., Delmas D., Lancon A., and Latruffe N. Transport of resveratrol, a cancer chemopreventive agent, to cellular targets: plasmatic protein binding and cell uptake. Biochem. Pharmacol. 68 (2004) 1113-1118
33. Jarolim S., Millen J., Heeren G., Laun P., Goldfarb D.S., and Breitenbach M. A novel assay for replicative lifespan in Saccharomyces cerevisiae. FEMS Yeast Res. 5 (2004) 169-177
34. King R.E., Bomser J.A., and Min D.B. Bioactivity of resveratrol. CRFSFS 5 (2006) 65-70
35. Klis F.M., Mol P., Hellingwerf K., and Brul S. Dynamics of cell wall structure in Saccharomyces cerevisiae. FEMS Microbiol. Rev. 26 (2002) 239-256
36. Krasnow M.N., and Murphy T.M. Polyphenol glucosylating activity in cell suspensions of grape (Vitis vinifera). J. Agric. Food Chem. 52 (2004) 3467-3472
37. Kroll J., Rawel H., and Rohn S. A review: reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds. Food Sci. Technol. Res. 9 (2003) 205-218
38. Lancon A., Delmas D., Osman H., Thénot J.P., Jannin B., and Latruffe N. Human hepatic cell uptake of resveratrol: involvement of both passive diffusion and carrier-mediated process. Biochem. Biophys. Res. Commun. 316 (2004) 1132-1137
39. Lania-Pietrzak B., Hendrich A.B., and Michalak K. Perturbation of model lipid membrane structure by resveratrol. Curr. Topics Biophys. 28 (2004) 17-60
40. Larionova N.V., Kazanskaya N.F., Larionova N.I., Ponchel G., and Duchene D. Preparation and characterization of microencapsulated proteinase inhibitor aprotinin. Biochemistry (Moscow) 64 (1999) 857-862
41. Li Y.B., Cao Z.X., and Zhu H. Upregulation of endogenous antioxidants and phase 2 enzymes by the red wine polyphenol, resveratrol in cultured aortic smooth muscle cells leads to cytoprotection against oxidative and electrophilic stress. Pharmacol. Res. 53 (2006) 6-15
42. Lipke P.N., and Ovalle R. Cell wall architecture in yeast: new structure and new challenges. J. Bacteriol. 180 (1998) 3735-3740
43. López-Nicolás J.M., Núñez-Delicado E., Pérez-López A.J., Barrachina A.C., and Cuadra-Crespo P. Determination of stoichiometric coefficients and apparent formation constants for β-cyclodextrin complexes of trans-resveratrol using reversed-phase liquid chromatography. J. Chromatogr. A 1135 (2006) 158-165
44. Luan X., Skupin M., Siepmann J., and Bodmeier R. Key parameters affecting the initial release (burst) and encapsulation efficiency of peptide-containing poly(lactide-co-glycolide) microparticles. Int. J. Pharm. 324 (2006) 168-175
45. Luzi C., Brisdelli F., Cinque B., Cifone G., and Bozzi A. Differential sensitivity to resveratrol -induced apoptosis of human chronic myeloid (K562) and acute lymphoblastic (HSB-2) leukemia cells. Biochem. Pharmacol. 68 (2004) 2019-2030
46. Maisuthisakul P., Pongsawatmanit R., and Gordon M.H. Characterization of the phytochemicals and antioxidant properties of extracts from Teaw (Cratoxylum formosum Dyer). Food Chem. 100 (2007) 1620-1629
47. Martin A.R., Villegas I., La Casa C., and de la Lastra C.A. Resveratrol, a polyphenol found in grapes, suppresses oxidative damage and stimulates apoptosis during early colonic inflammation in rats. Biochem. Pharmacol. 67 (2004) 1399-1410
48. Matsuoka A., Takeshita K., Furuta A., Ozaki M., Fukuhara K., and Miyata N. The 4′-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol. Mutat. Res. 521 (2002) 29-35
49. Nam J.B., Ryu J.H., Kim J.W., Chang I.S., and Suh K.D. Stabilization of resveratrol immobilized in monodisperse cyano-functionalized porous polymeric microspheres. Polymer 46 (2005) 8956-8963
50. Nelson G. Application of microencapsulation in textiles. Int. J. Pharm. 242 (2002) 55-62
51. Nelson, G., Wales, D.S., Sagar, B.S., 1991. Treating Materials. European Patent, EP 0511 258, B1.
52. Nonomura S., Kanagawa H., and Makimoto A. Chemical constituents of polygonaceous plants. I. Studies on the components of Ko-J O-Kon (Polygonum cuspidatum Sieb. Et Zucc.). Yakugaku Zasshi 83 (1963) 988-990
53. Norata G.D., Marchesi P., Passamonti S., Pirillo A., Violi F., and Catapano A.L. Anti-inflammatory and anti-atherogenic effects of cathechin, caffeic acid and trans-resveratrol in apolipoprotein E deficient mice. Atherosclerosis 191 (2007) 265-271
54. Normand V., Dardelle G., Bouquerand P.E., Nicolas L., and Johnston D. Flavor encapsulation in yeasts: limonene used as a model system for characterization of the release mechanism. J. Agric. Food Chem. 53 (2005) 7532-7543
55. Okada Y., and Okada M. Scavenging effect of water soluble proteins in broad beans on free radicals and active oxygen species. J. Agric. Food Chem. 46 (1998) 401-406
56. Olas B., and Wachowicz B. Resveratrol, a phenolic antioxidant with effects on blood platelet functions. Platelets 16 (2005) 251-260
57. Orallo F. Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Curr. Med. Chem. 13 (2006) 87-98
58. Pacifici G.M. Inhibition of human liver and duodenum sulfotransferases by drugs and dietary chemicals: a review of the literature. Int. J. Clin. Pharmacol. Ther. 42 (2004) 488-495
59. Pannell, N.A., 1990. Microencapsulation in microorganisms. European Patent, EP 0242 135, B1.
60. Piñeiro Z., Palma M., and Barroso C.G. Determination of trans-resveratrol in grapes by pressurised liquid extraction and fast high-performance liquid chromatography. J. Chromatogr. A 1110 (2006) 61-65
61. Pozo-Guisado E., Merino J.M., Mulero-Navarro S., Lorenzo-Benayas M.J., Centeno F., Alvarez-Barrientos A., and Femandez-Salguero P.A. Resveratrol-induced apoptosis in MCF-7 human breast cancer cells involves a caspase-independent mechanism with downregulation of Bcl-2 and NF-kappaB. Int. J. Cancer 115 (2005) 74-84
62. Regev-Shoshani G., Shoseyov O., Bilkis I., and Kerem Z. Glycosylation of resveratrol protects it from enzymic oxidation. Biochem. J. 374 (2003) 157-163
63. Renaud S., and de Lorgeril M. The French paradox: dietary factors and cigarette smoking-related health risks. Ann. NY Acad. Sci. 686 (1993) 299-309
64. Richard J.L. Coronary risk factors. The French paradox. Arch. Mal. Coeur Vaiss. 80 (1987) 17-21
65. Savouret J.F., and Quesne M. Resveratrol and cancer: a review. Biomed. Pharmacother. 56 (2002) 84-87
66. Scherrer R., Louden L., and Gerhardt P. Porosity of the yeast cell wall and membrane. J. Bacteriol. 118 (1974) 534-540
67. Schrooyen P.M.M., van der Meer R., and De Kruif C.G. Microencapsulation: its application in nutrition. Proc. Nutr. Soc. 60 (2001) 475-479
68. Shahidi F., and Han X.Q. Encapsulation of food ingredients. Crit. Rev. Food Sci. Nutr. 33 (1993) 501-547
69. Shenouda N.S., Zhou C., Browning J.D., Ansell P.J., Sakla M.S., Lubahn D.B., and Macdonald R.S. Phytoestrogens in common herbs regulate prostate cancer cell growth in vitro. Nutr. Cancer 49 (2004) 200-208
70. Shi G.R., Rao L.Q., Yu H.Z., Xiang H., Pen G.P., Long S., and Yang C. Yeast-cell-based microencapsulation of chlorogenic acid as a water-soluble antioxidant. J. Food Eng. 80 (2007) 1060-1067
71. Signorelli P., and Ghidoni R. Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J. Nutr. Biochem. 16 (2005) 449-466
72. Szabolcs A., Varga I.S., Varga C., Berkó A., Kaszaki J., Letoha T., Tiszlavicz L., Sári R., Lonovics J., and Takács T. Beneficial effect of resveratrol on cholecystokinin-induced experimental pancreatitis. Eur. J. Pharmacol. 532 (2006) 187-193
73. Trela B.C., and Waterhouse A.L. Resveratrol: isomeric molarabsorptivities and stability. J. Agric. Food Chem. 44 (1996) 1253-1257
74. Ueda H., Ou D., Endo T., Nagase H., Tomono K., and Nagai T. Evaluation of a sulfobutyl ether beta-cyclodextrin as a solubilizing/stabilizing agent for several drugs. Drug Dev. Ind. Pharm. 24 (1998) 863-867
75. Ulrich S., Wolter F., and Stein J.M. Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis. Mol. Nutr. Food Res. 49 (2005) 452-461
76. Vastano B.C., Chen Y., Zhu N., Ho C.T., Zhou Z., and Rosen R.T. Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum. J. Agric. Food Chem. 48 (2000) 253-256
77. Walle T., Hsieh F., Delegge M.H., Oatis Jr. J.E., and Walle U.K. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 32 (2004) 1377-1382
78. Wenzel E., and Somoza V. Metabolism and bioavailability of trans-resveratrol. Mol. Nutr. Food Res. 49 (2005) 472-481
79. Wieder T., Prokop A., Bagci B., Essmann F., Bernicke D., Schulze-Osthoff K., Dorken B., Schmalz H.G., Daniel P.T., and Henze G. Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts. Leukemia 15 (2001) 1735-1742
80. Wu S.L., Yu L., Pan C.E., Jiao X.Y., Lv Y., Fu J., and Meng K.W. Apoptosis of lymphocytes in allograft in a rat liver transplantation model induced by resveratrol. Pharm. Res. 54 (2006) 19-23
81. Zlotnik H., Fernandez M.P., Bowers B., and Cabib E. Saccharomyces cerevisiae mannoproteins from an external cell wall layer that determines wall porosity. J. Bacteriol. 159 (1984) 1018-1026